The broad goal of this research is to develop methods for synthesizing novel classes of organic compounds which have unusual or interesting structural features and useful pharmacologic properties. Cyclohexadienones, methylenecyclopentenones and endoperoxides will be exploited as synthetic precursors of highly functionalized molecules, particularly those with epoxide, hydroxyl and amine functionality on five or six contiguous carbon atoms. Such molecules are expected to show anti-viral, anti-cancer and/or antibiotic activity. A novel class of polynuclear heteroaromatic compounds will be prepared which have two or three heterocyclic rings (for example, thiophene, pyrrole or furan) fused to a carbocyclic ring in a unique way. These electron-rich substances and their derivatives are expected to show unusual properties, among them a propensity for charge and electron transfer. Their pharmacologic properties will be tested. Throughout this work, the photochemical as well as ground state chemistry of new substances will be studied, with the dual objective of discovering new and synthetically useful photochemical reactions and of synthesizing new classes of compounds.